JPH04984B2 - - Google Patents
Info
- Publication number
- JPH04984B2 JPH04984B2 JP5542683A JP5542683A JPH04984B2 JP H04984 B2 JPH04984 B2 JP H04984B2 JP 5542683 A JP5542683 A JP 5542683A JP 5542683 A JP5542683 A JP 5542683A JP H04984 B2 JPH04984 B2 JP H04984B2
- Authority
- JP
- Japan
- Prior art keywords
- methylquinoline
- yield
- mol
- quinolines
- thionyl chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 36
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 33
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 22
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 17
- 150000003248 quinolines Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-methylquinoline Chemical compound C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- XCMAYGDQKTWICK-UHFFFAOYSA-N 3-methylquinoline-8-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC2=CC(C)=CN=C21 XCMAYGDQKTWICK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- HTAMTFRQJZCNAH-UHFFFAOYSA-N 3-methylquinoline-5-sulfonyl chloride Chemical compound C1=CC=C(S(Cl)(=O)=O)C2=CC(C)=CN=C21 HTAMTFRQJZCNAH-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- QZNQYKSCUCTMBZ-UHFFFAOYSA-N 2-methylquinoline-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=NC(C)=CC=C21 QZNQYKSCUCTMBZ-UHFFFAOYSA-N 0.000 description 1
- OPUILGVLAQHFHX-UHFFFAOYSA-N 3-methylquinoline-2-sulfonic acid Chemical compound C1=CC=C2N=C(S(O)(=O)=O)C(C)=CC2=C1 OPUILGVLAQHFHX-UHFFFAOYSA-N 0.000 description 1
- KNYYFFXETCFCNE-UHFFFAOYSA-N 3-methylquinoline-5-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(C)=CN=C21 KNYYFFXETCFCNE-UHFFFAOYSA-N 0.000 description 1
- BTBNYOKJERLLQI-UHFFFAOYSA-N 3-methylquinoline-8-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(C)=CN=C21 BTBNYOKJERLLQI-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000005957 chlorosulfonylation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5542683A JPS59184161A (ja) | 1983-03-31 | 1983-03-31 | 塩化スルホニル類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5542683A JPS59184161A (ja) | 1983-03-31 | 1983-03-31 | 塩化スルホニル類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59184161A JPS59184161A (ja) | 1984-10-19 |
| JPH04984B2 true JPH04984B2 (fr) | 1992-01-09 |
Family
ID=12998250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5542683A Granted JPS59184161A (ja) | 1983-03-31 | 1983-03-31 | 塩化スルホニル類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59184161A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4233601A1 (de) * | 1992-10-06 | 1994-04-07 | Bayer Ag | 3-substituierte Chinolin-5-carbonsäuren |
| CN100422154C (zh) * | 2006-04-07 | 2008-10-01 | 北京成宇化工有限公司 | 3-甲基喹啉-8-磺酰氯的制备方法 |
| CN113563234B (zh) * | 2021-07-05 | 2023-06-23 | 佛山市南海北沙制药有限公司 | 一种对乙酰氨基苯磺酰氯的生产工艺 |
-
1983
- 1983-03-31 JP JP5542683A patent/JPS59184161A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59184161A (ja) | 1984-10-19 |
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